Synthesis, photophysical properties and photocytotoxicity of mono-, di-, tri- and tetra-glucosylated fluorophenylporphyrins

In order to explore the effect of substitution patterns on the photocytotoxicity of glycoconjugated porphyrins, we synthesized and characterized a ‘complete set’ of tetrakis(perfluorophenyl)porphyrins having β-d-glucopyranosylthio groups on the phenyl ring. Among five possible derivatives, trans-substituted S-glucosylated porphyrin trans-2OH exerted outstanding photocytotoxicity (EC50 value was <5 nM) in HeLa cells. The excellent photocytotoxicity of trans-2OH was found to be attributable to several factors, namely high optical transition probability in aqueous media, efficient type I photoreactions and enhanced cellular uptake.

We synthesized five possible perfluorophenylporphyrins having S-glucopyranosyl groups. The effect of the glycosylation patterns on the photocytotoxicity was discussed on the basis of photophysical properties as well as cellular uptake in HeLa cells.Figure optionsDownload as PowerPoint slide